5 founder mistakes that keep your lawyer up at night

1. Giving away board seats to convertible note holder investors

Finding the right partner to invest in your business out of the gate is paramount to the success of a start-up (particularly) through its infancy stage. If your initial investors are conditioning their participation in your “friends and family” bridge round on receipt of a board seat, that should serve as a red flag. Your venture’s earliest investors, if experienced, should understand the fact that the founding team requires a maximum amount of flexibility at the board level as the company is coming out of inception and through its bridge financing. Adding an outside investor influence is more appropriate at the time of the company’s initial equity financing. Disrupting that equilibrium beforehand can cause problems for founders (too many cooks in the kitchen) and most importantly, may slow the company’s ability to achieve desired growth (forcing founders to chase after partially committed investors). And don’t buy the “but we want to help more than just giving you capital” argument. If that’s the case, set up a quarterly scheduled call or coffee meeting.

2. Issuing founders convertible note

Common Stock should be held by founders/management/employees and preferred stock should be held by investors. Any disruption of that fact inevitably introduces complexity as it relates to establishing an appropriate and unbiased governance structure of a company. For founders who have dedicated significant $ resources before outside capital becomes available, there is a temptation to “honor” that debt and roll it into the first convertible note round. The terms of that convertible note round, however, will undoubtedly have a conversion mechanism whereby investment in the convertible note ultimately converts into the preferred stock sold to investors in the initial equity round. Suggestion: instead of piggybacking the founder’s loan through that convertible note instrument, founders should consider documenting their loan instead as a straight promissory note (without a conversion feature) that would get repaid at some future trigger date.   

3. Not getting assignment of IP agreements from contributors out of the gate

This is one I see too often. At the time of engaging lawyers to legally form an entity that will house a product that you and your 2 other co-founders have been dedicating time to over the last 3 months, you get asked by your attorney to have everyone who has contributed to the IP of the company in the prior 3 months to execute an assignment of IP agreement. The problem: there was a 4th individual who was a part of the early conception stage but disappeared on you last week because they disagreed with the direction of the product build. Now they won’t answer your emails. The takeaway: if you are leaning on the contributions of individuals other than yourself out of the gate, immediately forming the legal entity and putting all the IP created in the company is paramount to not finding yourself in this situation.    

4. Spending too much time coming up with special vesting arrangements for co-founders

You are not only an incredibly intelligent individual but you are brave enough to put everything on the line to pursue an idea you feel passionate about. That fact is what gets me up in the morning to work and why I love my job so much. BUT, nothing is more frustrating that seeing you divert your efforts and intelligence away from building your company to instead coming up with novel vesting schedule schemes for you and your co-founders. 9 out of 10 times it will end up being a waste of the company’s money and time. Stick to what you do really well. Building companies. Not unique vesting schedules.

5. Not filing 83(b)s

And… I saved the best for last. You go through the incorporation process with your lawyers. You form your entity, you finalize equity documents and then you are off to the races building your company. You are feeling really good until you find out that your lawyer (and most likely their paralegal or junior associate) becomes complacent and fails to file or remind you to file your 83(b) election for the un-vested equity you received at incorporation. This is the ultimate mistake you and your lawyer can make out of the gate. If a founder does not make an 83(b) election, in any taxable year in which equity vests, the founder will be required to include in his/her gross income as ordinary income the delta between the fair market value of the equity at the time such equity vests and the price he/she paid for the equity.  As a result, income that likely would have been taxable at capital gain rates upon sale if the founder had made an 83(b) election would be taxable at ordinary income rates upon vesting. Yikes. 

The Convertible Noteholder Standoff

For founders, raising that first equity round is a true milestone. It is not only an opportunity to bring in meaningful dollars from professional investors to fuel a start-up’s growth but, if you have had outstanding notes running interest since the early days coming out of inception, it also serves as a chance to clean up your company’s cap table by converting outstanding convertible instruments in connection with the round. With angel investors’ broad adoption and comfort of investing into early stage companies through convertible instruments, companies are delaying the need to sell preferred stock in an equity round, in some cases, for the first couple years of a company’s development. The fallout from this reality, however, is that when you do head toward closing that first equity financing, a founder will have the task of coordinating with the (sometimes, many) noteholders in connection with the conversion of those noteholders’ outstanding notes.

With a syndicated noteholder base, the risks of holdout (or unreachable) noteholders is elevated and without collection of all signatures from that constituency in connection with the equity round, the new money investors in the financing will inevitably be spooked. To combat the potential negative effects and risks of a “standoff” down the road at the time of the equity financing, initially when preparing and issuing your convertible notes, your counsel should be advising you on the appropriate language to include in the instrument to ensure there is zero room for interpretation in the event the noteholder does not provide its signature at the time of a triggering financing and resulting automatic conversion. Without an air tight documented mechanism, you will otherwise risk taking the “automatic” out of automatic conversion and open up potential delay in the closing of you ever-so-important equity financing.  

Amending Convertible Notes in connection with a Qualified Financing: A Word of Caution.

For some time convertible notes have been, and remain to this day, the preferred vehicle for an early stage company raising initial capital. A known commodity in the marketplace, the barriers and expenses of closing note bridge rounds continue to be less than opting for the sale of an equity security. What early stage investors might not be aware of, however, is a trend gaining steam of late – as company valuations increase in earlier investment rounds, a growing number of sophisticated lead investors in “Qualified Financings” (ie the company’s equity financing that triggers conversion of the notes) are applying increasing pressure to condition their investment in the round on the company amending the terms of their outstanding convertible notes to carve back a portion of the economic windfall received by noteholders in the Qualified Financing.

Setting the stage: The terms of a vast majority of convertible promissory notes in the marketplace provide that a note investor’s principal (plus interest) under a convertible note will, at a Qualified Financing, convert into the security sold in the Qualified Financing (ie Series Seed or Series A preferred stock) at the lower of (i) a discount to the price in the Qualified Financing or (ii) a pre-negotiated capped valuation.

The economic problem: Particularly in early friends and family note rounds, the pre-negotiated capped valuations are often times significantly lower than the valuation in the Qualified Financing. If the terms of the note are honored as-is, note investors would get the benefit of receiving not only the actual dollars (plus interest) invested under the note in the form of the same shares issued in the Qualified Financing, but also the (in most cases, material) discount premium as a result of the discount or capped price. This became known as the “phantom liquidation preference problem” – referencing the layered liquidation preference received on the lot of shares which had been converted into as a direct result of the cap piece of the conversion. 

The Lead investor’s fix: Condition the closing of the Qualified Financing on the company obtaining the requisite approval from their noteholders to amend the notes to either (i) convert the discount portion of shares received in the round into common stock, as opposed to preferred stock or (ii) convert into a shadow series of preferred with the same rights as the preferred stock sold to new money investors in the Qualified Financing with the exception that the liquidation preference on the shadow security is carved back to the conversion price at which the notes converted in the round.

The note investor’s dilemma: Either (A) don’t approve the amendment and the company you are invested in doesn’t receive the capital to continue operations or (B) approve the amendment and lose out at the deal originally bargained for which credited the note holder for making a risky investment in the first place.

The Conclusion for early stage investors: The lead investors in a Qualified Financing wields significant power in setting the terms for the new money round, which includes potentially forcing early note investors to adopt alterations to their initial note conversion deal. As an early stage note investor, however, there are precision drafting protections your lawyer can help institute at the time of the original investment which have the effect of returning at least some of the power back in the hands of a company’s earliest investors at the time of conversion. In any event, don’t be naïve: the suppressed valuation cap you successfully negotiate for in your note investment documents, if left naked, may end up taking on a much different economic outcome than you originally bargained for.

5 Pitfalls To Avoid When Building Out Your Advisory Board

One of the first conversations I have with founders following the incorporation process is around forming and filling an advisory board. As a founder, surrounding yourself with knowledgeable, connected and committed players can add significant value for your start-up out of the gate. On the flip side, there are uniform mistakes founders often make that end up hurting their company (and cap table). Here are 5 of them:

1.       Too many advisors, too soon.

Coming out of inception can be a scary time for a founder, particularly if this the first time at the rodeo. There can be a resulting temptation to get as many advisors involved with your company as soon as possible. The thinking being that, given the relatively cheap costs of an advisor (often just a modest equity grant; see discussion below), your start-up doesn’t need to give up too much to get in return the cache of attaching a strong roster of big names toyour company. A founder’s concentration, however, should be on building meaningful relationships with a small handful of trusted advisors that are going to be available and committed to the success of your company (and, on the flip side, that you will have time to leverage). Additionally, what your company might need today (e.g. advisor with particular industry expertise and/or connections to VCs) is not what it will need in the future (e.g. advisor with experience building commercial relationships or connections to strategic investors/acquirers). Remember, nothing precludes you from adding additional advisors to your company’s roster at those future inflection points….which is when you will be able to get the most out of the relationship.

2.       Defining your advisor’s responsibilities too broadly.

The most sought after advisors are often time the busiest advisors. It is important to set expectations at the outset by establishing discreet parameters for an advisor’s responsibilities. As opposed to the loosely defined roles: “general advising services,” “periodic check-ins,” etc. Think: quarterly calls, review of deck/investor pitch, make # of introductions, etc…the types of metrics that you can hold the advisor accountable for and which will help prevent the “disappearing” advisor problem. Advisors will appreciate a more defined role and set of expectations so they can pre-schedule their services into their busy calendar. 

3.       Giving away too much equity.

I’ve talked with a number of high profile advisors who are constantly being asked to formally advise tech start-ups. One of the pieces of feedback from them is that they are often times amazed at how much a start-up is willing to give-up in equity for only a small amount in return. As a founder, it is easy to get excited about adding that star name advisor to your advisory board but don’t deviate from market expectation. Depending on what services your company will receive, expect to give up anywhere from 0.10% - 0.50% of the fully diluted capitalization of your company. Anything more begins to look expensive (and may be questioned as such by your investors).

4.       Getting vesting wrong.

A founder’s instinct may be to set a service provider's vesting period as long as possible to maximize value over a longer period of time. When it comes to advisors, however, that is most often the wrong approach. Advisors typically have a shelf life as to their value accretion. VCs absolutely appreciate the fact that these advisor relationships take their course over a much shorter period than the standard 4-year employee vest period. And that period is typically no longer than 2 years. So instead of diluting value over a longer vest period, the question a founder should be asking is how to maximize value within that shorter window.  

5.       Don’t judge an advisor by its cover.

Picking the right advisor is not a “one-glove-fits-all" exercise. It can be tricky to anticipate which advisor relationship will ultimately prove to be fruitful. That said, there are initial signs that a founder should certainly not ignore. If the engagement process takes weeks to close out (perhaps because the prospect keeps disappearing on you or they over negotiate the arrangement, etc) or you find yourself being too shy to flesh out the details of what you might expect from the relationship (perhaps because you are concerned you would be bothering the prospect or overburdening them), chances are its not the right fit. A star advisor looks great on the final slide of your pitch deck but an advisory board alone will not be the determining factor for a VC to give you money. Results are. Choose wisely.

Outsourcing Software Development and the IP Conundrum

Cash burn. Two words that keep founders up at night and inevitably force them to at least consider outsourcing all or a portion of their start-up’s software development to an independent contractor (“IC”), as opposed to incurring the costs of adding another technical co-founder or employee on payroll (not to mention the time and energy those searches take). With more and more development shops/moonlighting developers to tap into in the marketplace (domestically and abroad), its no surprise that more and more start-ups are turning to outsourcing opportunities.  

If you are beginning to head down this path, there are some key considerations to discuss with your attorney at the outset, none more critical, however, than ensuring that there are no roadblocks to your company owning outright the IP in the work delivered by the IC. Anything short of that fact will result in a surefire way to jeopardize your company’s ability to close future financings/exit without exposure to future claims of IP infringement. So you might be thinking: “I am all set, the form consulting agreement my lawyer provided me has clear language that the IC’s deliverables are work for hire and therefore assigned (along with all associated IP) to my company.” Think again. 

The classic example - The IC you engage is moonlighting as a part-time developer, but has a full-time day job as an employee at Company X. The IC’s overreaching employment agreement with Company X states that any software created while employed at Company X, belongs to Company X, regardless of whether the software is developed “on the side” or related to the current business of Company X. You never establish this fact upfront with the IC, the IC develops the software, and on the eve of closing your Series A financing, you receive a letter from Company X claiming they own the IP delivered by your IC. Yikes. 

TAKE AWAY: When you are considering engaging an IC, it is absolutely critical to ask up front whether the IC is under any other arrangement (employment or otherwise) with a third party that would in any way restrict the IC’s ability to freely assign to your company the deliverables and associated IP created on your behalf. If so, your alarm should go off...

...time to call your lawyer! 

NDAs. One glove does not fit all.

The Non-Disclosure Agreement has been commoditized to the point that start-up companies looking to save on legal costs have found ways to get comfortable executing these types of agreements without bothering to run them by their attorney, particularly in light of the fact that, from a founder’s perspective, the NDA serves as a major barrier to engage in potentially life changing conversations with a possible commercial partner, investor, advisor, or acquirer. Maybe your lawyer provided you with a form in the past or perhaps given the "mutual" nature of the form NDA presented by the counter party, you’ve concluded that the risks of signing are minimal. 

Depending on the context of when/why you are protecting your information as confidential, however, the form in play may be missing critical terms that might not be so obvious at first. For example, discussions leading up to a potential: 

  • sale of the company – does your NDA contain a non-solicit of employees?
  • partnership or other commercial relationship – does your NDA include protection on reverse engineering?
  • engagement of a high profile advisor or consultant– does your NDA carve out the company’s ability to disclose the existence of the engagement through a press release or pitch deck?
  • investment in a company – from the VC’s perspective, does the NDA make clear that your fund will not be restricted in any way from investing in companies in a competing space?

It is easy for a founder to gloss over the NDA but doing so may prove costly in the long run.

Wire Fraud on the Rise… Could the VC Community Be Hit Next?

It has been widely reported that cyber criminals are hijacking real estate transactions by finding increasingly sophisticated ways to intercept and make alterations to wiring instructions being distributed between parties leading up to a real estate closing, resulting in the wiring party being duped into releasing funds to an alternative (and often times, off shore) bank account. Over the last year, hackers are starting to apply the same techniques to prey on the venture capital community and financings transactions. Read here

This got me thinking about the standard practice for how venture financings are closed, specifically the process around how wiring instructions are shared between a company and its soon-to-be investors as well as the particular ripeness of the industry to be targeted by similar scams.  

It is customary that leading up to the final moments before a VC transaction closing, lawyers find themselves caught in the middle of coordinating distribution of final deal documents along with the company’s wiring instructions. Here’s how it typically unfolds: (1) a company will email its lawyers the company's wiring instructions to distribute along with executed documents and the filed charter, (2) the company's lawyers turn around and send a closing email, which contains those instructions, to the Investor’s lawyers, (3) Investor’s lawyers then forward along to their client with confirmation that the closing conditions have been met and the wire should be released. By my count that is 3 emails sent containing wiring instructions…. which is 3 emails too many!

It is time for lawyers to insist that the parties to a transaction take much more calculated steps to limit the risks associated with this particular style of cyber crime. Founders and VCs should communicate directly on wiring instructions, separate from the lawyers' deal document distribution, through secured means other than email and, prior to wiring any funds, the VC (or a member of their finance team) should contact the company by phone and confirm that the wiring information sent over email is accurate. In my experience, this isn’t common practice. But it should be.

Nascent App Dev Shops: The ins and outs of taking equity in your clients

Last month I was sitting down for coffee with the CTO of one of the most successful app development shops in Boston. He confirmed what I had suspected –his firm, like many of his largest competitors in the space, resisted the temptation of taking equity in their clients in lieu of service fees. Unlike venture backed product based companies, for app dev shops and other service based companies, leveraging investor capital to grow your company is much more rare, and rather, your fee compensation is the lifeline of your business. But for you founders of newly formed app dev shops, agreeing to take all or a portion of your fees in the form of equity, if you can stomach the risk, might end up being the difference maker in winning your next job from an early stage start-up that is preserving burn at all costs. Here are a few alternative forms of consideration you might contemplate taking from your potential clients, and the upside and downside of each:

Convertible Notes

If the start-up you are contracting with has an open bridge round whereby the company is taking investment in exchange for the issuance of convertible notes, you might consider exchanging services for principal in a note issued in the round.

Upside: Convertible notes have the benefit of running interest (typically at a rate of 3-8%) and, at conversion, noteholders enjoy a steep discount to the price paid by new investors for the security into which the noteholders debt converts in the next equity round. 

Downside: There are plenty of start-ups that are successful raising an initial friends and family bridge note round but aren’t able to build a business which attracts enough interest from institutional investors to successfully close an equity round.


Regardless of whether your potential client has an open bridge round, the YCombinator SAFE security is flexible to allow for a single SAFE to be issued to an investor, or in this case, a service provider, without the need for your potential client to open a broader round of financing.  

Upside: Although there is no interest running on the note, SAFE holders, similar to noteholders, enjoy the same steep discount to the price paid by new investors for the security into which the SAFE holder’s purchase amount converts in the next equity round.

Downside: Similar to the risks of a noteholder, there is a chance the SAFE never converts and you are left holding an illiquid, equity security (junior in payment to debt) in a failing company.


If the potential client prefers not to issue their service providers an investment instrument in exchange for services, an alternative form of compensation can come by way of a warrant. A warrant is a security which gives a holder the right to purchase a certain number of shares (common or preferred), within a defined period, at a set price equal to the fair market value of the underlying security on the date of grant of the warrant. The idea, similar to a stock option held by an employee, is that as the value of the underlying security increases, the warrant holder will enjoy the delta over that set price stated in the warrant and the ultimate value (most likely at a sale of the company).

Upside: The issuance of a warrant is not contingent on the company having an open bridge round and the warrant security will provide for a cashless mechanism whereby the warrant holder will never have to actually come out of pocket to enjoy the increase in value of the warrant.

Downside: The term of a warrant is typically 10 years and, even if the potential client is able to sell their company within that time frame, there is always the risk that the valuation of the company in such sale may not be high enough for the warrant to be in the money.

Seed Investors: read this if you care about your pro rata!

Pro Rata Right to Participate. Preemptive Right. Participation Right. Call it what you may but this is one of the most important economic rights that attach to the preferred security received by a seed investor when making an investment into a portfolio company. For early stage investors, particularly those funds with limitations on their ability to cut larger checks to put them in the running to lead future rounds, preserving the right to participate in a portfolio company’s follow-on financing is paramount to future returns. Here is a word of caution for you seed stage investors (and your lawyers): Don’t risk being shut out of your participation right by missing a simple, yet key, technical drafting feature in your deal documents. The following anecdote sheds light on how that could happen:

Recently I was representing a VC in a subsequent round of financing for one of their portfolio companies. The round was being led by a strategic investor that had not previously invested in the company. My client and certain other existing investors planned to exercise their right to participate in the deal pro rata through a subsequent closing but, as is standard in financings, at the initial closing, existing stockholders, including my client, agreed to waive their contractual right to participate pro rata in the round, with the understanding that they would participate nonetheless. Note to the reader: This waiver is almost always solicited by the company, regardless of whether the company and new investor intend to honor the right of existing stockholders to participate, as it removes the need for the company to comply with the hoops and notice periods set out under the existing preemptive rights provision and, by doing so, a company avoids further delay on closing the current financing. Existing investors end up getting comfortable consenting to the waiver so long as the handshake business deal allows them to participate for an amount at least as large as what they were contractually entitled to had they not waived. 

So back to the deal I was working on….when the deal documents were distributed for final sign off, the lead investor had included language which would have subject participation in subsequent closings to that lead investor’s approval. Cue the lawyer’s alarm! With the participation waiver in hand at the initial closing and the lead investor’s ability to block who the company could accept as investors in subsequent closings, that set up a situation where existing investors could have technically been shut out of investing in the deal all together, in spite of the company’s desire to let them participate. Lesson for seed investors: ensure that your deal documents expressly carve out existing investors from lead investor’s block on who participates in subsequent closings, otherwise risk losing your ability to invest pro rata……and getting burned!

Getting ready for an equity raise? Read this if you want to save time and money on legal fees.

I am working with a handful of companies expecting to raise an equity round in the next couple months. In some cases, it will be a company’s first real fundraise, with prior investment coming through a bridge round (notes, SAFES, etc). In other cases, it will be a Seed-2 or A round. Regardless, It is a nerve racking time for a founder/management team and with everything else on your mind, ensuring your company’s books and records are in order from a legal perspective is most likely not high on the to-do list to prepare for the financing, but it should be. Here are 3 easy steps you and your team should be taking weeks before you execute a term sheet to ensure you will cut down on deal timeline and, most importantly, legal fees.

1) Start Populating your Dataroom

Often times your lawyers will have records relating to incorporation, stock grants, board consents, etc. but there are non-legal categories of information which your lead investor’s counsel will absolutely request in the course of their diligence which you or your team members will be better equipped to provide (as opposed to your lawyers), like, for example, commercial agreements with customers, financials, schedule of IP assets and descriptions of third-party source code that the company has incorporated in its products, etc.  A member of the team should be taking the time to organize, gather and populate the dataroom before the term sheet is signed so when the diligence request comes in from investor’s counsel, all you have to do is send the invitation. Leaving this task in the hands of your lawyer becomes inefficient and time consuming. So do yourself a favor, open up a dropbox account (a now totally accepted venue for investors and their counsel) and take control of creating/populating your dataroom. Not doing so will be costly.   

2) Start Collecting Information for Disclosure Schedules

One of the key tasks of a junior associate in connection with a financing is guiding the disclosure schedule process. Often they invite a kick-off call with the client early in the transaction process whereby the associate spends the time (and your company’s money) to hold your hand and give you instruction on how to populate the disclosures in response to the reps and warranties in the stock purchase agreement. Here is a secret - you can save yourself the pain of that call by going to NVCA’s (National Venture Capital Association) website, download the form Stock Purchase Agreement (for free) and read through the reps and warranties (Section 2 of the form Stock Purchase Agreement) in close detail before the term sheet is even signed. To the extent you have an exception to a rep or the rep calls for you to disclose certain information, jot that disclosure down (informally is fine) on a piece of paper. 9 times out of 10 the reps that make it into the Purchase Agreement in your deal will look very similar, if not identical, as the reps and warranties are rarely negotiated heavily in the context of an early stage equity financing. Hand that list of disclosures over to your lawyer and they will be impressed. More importantly, you’ve just saved yourself a 2 hour call (at least) with a junior associate after the deal is in full swing. Woohoo!

3) Start Cozyin’ up with your Cap Table

Arguably the most important step you can take to save yourself a big headache heading into your financing is knowing your current cap table inside and out. It is your chance to start your relationship off on the right foot with your lead investor and helps you and your lawyers with organizing for the diligence process and preparing for drafting deal documents, as well as your counsel’s opinion (which will mostly require your lawyers to opine on the number of securities you have issued up until the financing). So go down each cell in your cap table well before your financing, ensure everyone that has received equity is on there and that anyone who is on there is being shown as receiving the right amount. Sounds simple enough but I can’t tell you how many times lawyers are left with this job. And trust me, it can get costly.